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Villas in Caribbean and Estates - Holiday Lettings - Holiday Rentals Caribbean

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17,528 Holiday homes

Holiday hotel apartment with shared pool in Dominican Republic

Puerto Plata hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £58 / night

£405 / week

1 / 44

Home rental in Caribbean with shared pool, golf nearby

Portmore house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing” To start, the location is great. Being in a gated community it made my family feel extremely safe. The house was clean, both rooms are big and well decorated with A/C. The kitchen made me feel at home large and spacious with all the basic necessities. The Wi-Fi was on point, never missed an email or my connection on social media. Needless to say, Mr Henry was great to work with. I will recommend this house to all my friends and family. Thank you Mr Henry.

from £89 / night

£567 / week

1 / 34

Caribbean holiday condo accommodation

Soufriere condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £95 / night

£630 / week

1 / 40

Curaçao holiday apartment rental

Willemstad apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £35 / night

£240 / week

1 / 10

Caribbean holiday home rental

Bridgetown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £180 / night

£1,079 / week

1 / 11

Holiday bungalow in Caribbean

North Caicos bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £113 / night

£787 / week

1 / 66

Holiday studio with shared pool in Guadeloupe

Deshaies studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £113 / night

£788 / week

1 / 44

Holiday apartment rental

Le Diamant apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £105 / night

£734 / week

1 / 18

Holiday studio in Caribbean

Sainte-Anne studio

  • Studio
  • 1 bathroom
  • sleeps 3

from £79 / night

£549 / week

1 / 21

Holiday bungalow in Caribbean

Saint Francois bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£610 / week

1 / 22

Holiday apartment with shared pool in Caribbean

Sainte-Anne apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £79 / night

£549 / week

1 / 19

Holiday apartment in Caribbean

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £72 / night

£504 / week

1 / 12

Holiday bungalow rental

Saint Francois bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£610 / week

1 / 21

Holiday bungalow with golf nearby in Caribbean

Saint Francois bungalow

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £124 / night

£864 / week

1 / 21

Penthouse rental in Caribbean

Cabarete penthouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £116 / night

£812 / week

1 / 17

Holiday apartment rental

Kralendijk apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £81 / night

£567 / week

1 / 26

Holiday villa in Caribbean

Frigate Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £158 / night

£1,888 / week

1 / 22

Caribbean holiday condo rental

Puerto Plata condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £146 / night

£1,020 / week

1 / 5

Caribbean holiday condo rental

Puerto Plata condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £146 / night

£1,020 / week

1 / 7

Holiday villa with swimming pool in Dominican Republic

Bavaro villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

from £1,349 / night

£9,440 / week

1 / 20

Caribbean holiday bungalow rental

Saint-Claude bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £137 / night

£823 / week

1 / 10

Barbados holiday apartment rental

Maxwell apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £99 / night

£693 / week

1 / 26

Holiday home with shared pool in Bahamas

Freeport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £135 / night

£944 / week

1 / 13

Holiday villa with swimming pool in St Martin / St Maarten

Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £415 / night

£2,902 - £7,459 / week

1 / 28

Holiday private room in Caribbean

Bouillante private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£610 / week

1 / 4

Caribbean holiday private room rental

Bouillante private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £117 / night

£816 / week

1 / 4

Caribbean holiday private room rental

Bouillante private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£610 / week

1 / 5

Holiday apartment with shared pool, golf nearby in Caribbean

Saint Francois apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £87 / night

£603 / week

1 / 18

Holiday apartment with shared pool in Caribbean

Puerto Plata apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £47 / night

£324 / week

1 / 8

Holiday apartment rental

Black Rock apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £77 / night

£535 / week

1 / 30

Holiday condo with shared pool in Caribbean

Cabo Rojo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £129 / night

£675 / week

1 / 17

Caribbean holiday apartment rental

Sainte-Anne apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £49 / night

£343 / week

1 / 10

Holiday home in Caribbean

Rincon house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £225 / night

£1,574 / week

1 / 18

Villa rental in Caribbean with shared pool

Terres Basses villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

from £765 / night

£5,350 / week

1 / 45

Holiday home rental

Marigot Bay house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £134 / night

£938 / week

1 / 25

Holiday studio with shared pool in Martinique

Le Diamant studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £118 / night

£583 / week

1 / 22

Caribbean holiday condo rental

Puerto Plata condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £180 / night

£1,259 / week

1 / 8

Condo rental in Dominican Republic with shared pool

Puerto Plata condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

from £180 / night

£1,259 / week

1 / 10

Guadeloupe holiday apartment rental

Le Gosier apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £69 / night

£480 / week

1 / 14

Studio rental in Caribbean with shared pool

Puerto Plata studio

  • Studio
  • 2 bathrooms
  • sleeps 4

from £54 / night

£315 - £944 / week

1 / 6

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Caribbean holidays

Turquoise ocean, sun-bleached sand, peach-gold sunsets and the most easy-going people on the planet… the Caribbean is every inch the perfect tropical paradise. Saint Lucia, Antigua, Dominica, Barbuda, Hispaniola and over 700 more islands are waiting to steal your heart.

Beachside Bliss

Awarding the title of ‘best beach in the Caribbean’ is like deciding which diamond in the Crown Jewels sparkles the most. It’s a nigh-on impossible, yet dazzling experience. Grand Cayman’s seven-mile paradise is a good place to start, with water as clear as glass, and the luxurious capital of George Town a stone’s throw away. Other Caribbean beach havens include Jamaica’s Montego Bay and virtually anywhere on Saint Martin island.

Secret Treasures

But the Caribbean isn’t all beaches and blue topaz seas. If you can drag yourself away from the sand on Puerto Rico, you’ll discover the tropical rainforest of El Yunque National Forest. Explorers who venture inland on most islands will be rewarded with secluded waterfalls, like Dunn’s River Falls in Ocho Rios, Jamaica.

Sub-Marine Spectacular

Snorkelling in the azure seas of the Caribbean is incredible, not least because of the vivid colours on display. Shoals of shimmering fish dart between coral reefs beneath the waves and when you come up for air, forests and palm trees cover the coasts. It’s like someone has turned up the colour saturation on your television. Head to Antigua’s Stingray City, a marine life petting zoo, for a hands-on experience you’ll never forget.

Top Destination reviews

Fire fly cottage with ocean view
Beautiful peaceful stay

We were looking for a remote cabin in peace and this was the perfect place. Quiet, relaxing and in the countryside. The hosts Geneva and Sean were lovely and helpful and easy to communicate with. We will definitely be back when need a quiet getaway in nature … see more
Clean 1bedroom with a turquoise view
Unit 58..Marlon

It was a wonderful stay..clean and Marlon was so attentive when needed ! comfortable with beautiful views...I would rent again for sure ! No complaints at all... just what I needed ! … see more
Millennium Park Trincity Vacation Home
Safe, peaceful and quiet!

I booked this house for my parents to stay in April 2023. They had nothing but positive things to say about it. It's a nice quiet community that they felt very safe in. They are looking forward to coming back next year. Thank you Nicholas and Natalie! … see more
TRAVELERS' CHOICE AWARD Villa Sol 2 minute walk to the Caribbean Sea
Amazing house and fabulous owners

Where do I start, Jean and Harry greeted us at our arrival which we got there a bit earlier than expected but they allowed us to check in and gave us the tour of the home which was immaculate, beautiful and so spacious. They provided everything we needed and more. If I could give them stars ✨ I would. They are the most thoughtful, caring and genuine couple who cares for their guests. We can’t wait to return and spend more time at their lovely home see more
Beachfront Oversize Studio with Stunning View
Honeymooner’s Paradise

If you are looking for a romantic getaway, this is the place. We had an amazing stay at this location. The hosts were informative about the area, easy to reach and very friendly. The apartment was open and airy and very inviting. It is equipped with everything you need for the beach, and anything you might need to cook. The location is excellent, only several minutes from the airport and a few feet from the beach. The view is unmatched and the floor to ceiling windows offer an incredible view at all times. We can’t say enough about this place and definitely hope to stay again in the future. It is an excellent stay for couples.see more
Brand New Luxury 4 Bed, Ensuite Villa - Kokomo
Girl’s holiday

I have had several holidays in this beautiful villa, it as everything you could possibly imagine, you can be on the beach or at a beach bar in a 5 minute walk, you can watch the sunset on the beach every night if you wanted to,.The supermarket is also 5 minutes away ,so if you would like to sit outside the villa and enjoy a glass of wine and some lunch it is perfectly okay,see more

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